Ninja-level musicians’: Paul Simon is joined by an expert crew for his Homeward Bound show in Manchester.
Photograph: Gary Calton for the Observer

There may be 50 ways to leave your lover, but Paul Simon, it seems, requires 15 people to prise him away from his love of touring. The huge stage for the first night of the UK leg of his Homeward Bound farewell tour is crawling with ninja-level musicians. Many of them also sing, giving rise to a forest of microphone stands and – further into a 26-song set list – a South African-inspired 10-part (approximately) harmony on a knockout rendition of Diamonds on the Soles of Her Shoes.

This tour is taking the star, 76, on a foreign foray one last time before he steps back from a six-decade career. It’s not curtains though: Simon announced a new album, In the Blue Light, revisiting 10 classic tracks, for release on 7 September.

Clearly, farewell tours often end up as misselling scams, but Simon is the sort of upstanding tunesmith whose honesty you hate to question. Tonight he reminisces about the time he played a working men’s club in northern England in 1964: “This is probably my last chance to do it,” he quips. “‘Shut oop’!” he quotes, in a brusque accent that wavers gamely between Liverpool and Yorkshire, “‘You’ve ’ad your fun, you’ve played bingo, now shut up and give the ah-tist a go’.” On the question of north v south, he adds mischievously: “I shouldn’t divide the nation, but it’s better up here.”

If farewells imply the prospect of greatest hits karaoke, Simon is emphatically not that kind of guy

Inspired by that 1964-5 jaunt, and the platform at Widnes station “where the plaque keeps getting stolen”, the song Homeward Bound pined for Simon’s then girlfriend Kathy Chitty back in Essex where Simon was based at the very start of his solo career, thanks to a welcoming folk club in Brentwood. Previously, an embryonic Simon and Garfunkel had plied their wares as Tom and Jerry, but Simon the solo artist very much began in the folk clubs of England.

Homeward Bound nailed homesickness with easy grace, and tonight, it is rendered almost unadorned in the encore. But it is hard to square the melancholy of the song with the enthusiastic, border-spurning innovator Simon eventually became. His very earliest attempts at Brill Building hackery gave way to Simon and Garfunkel’s triumphal folk-pop formula, of which there is a generous helping tonight. At the opposite end of the set list from Homeward Bound, the duo’s hitchhiking song America kicks off the set almost too brashly, a pro rendition whose gaudy soprano sax solo bodes ill for the two hours to come. The next song, 50 Ways to Leave Your Lover, falls prey to the same slickness.

Thankfully, these are two of only a few tonal missteps, with a back catalogue spanning half a century given arresting new arrangements and restless life. If farewells imply the prospect of greatest hits karaoke, Simon is emphatically not that kind of guy, and Homeward Bound is not that kind of tour.

He is also clearly not the sort of American who scuttles home from abroad, aghast at blunt landlords and other exotica. The schism with Garfunkel – the frictions are detailed in Robert Hilburn’s recent authorised biography – restarted Simon’s solo career. The 70s and 80s brought a series of explorations featuring a United Nations of musical styles. Simon unfurls most of them in Manchester, from the reggae lilt of Mother and Child Reunion (1972), recorded in Jamaica, to the Graceland album’s sonic jaunts to western and South Africa.

Other destinations include Brazilian drumming and Mariachi horns before we loop back to Cajun zydeco on That Was Your Mother. Here, a percussionist plays a washboard tunic with scary metal gloves, someone pings a triangle, and the accordion blare prompts Simon into a nimble shimmy. Throughout, his arms help him sing the songs when his fingers aren’t playing them.

The packed stage at Manchester Arena last week. Photograph: Gary Calton for the Observer

Simon seems to glory in the lush sounds made by the mob around him. Present and correct are old timers like bassist Bakithi Kumalo – he of the famous plunked solo on You Can Call Me Al – and mutton-chopped co-lead guitarist Mark Stewart, on board since 1999. Most missed is longtime Simon guitarist Vincent Nguini, a silver-fingered mainstay since 1990 whom a Brazilian faith healer could not save from liver cancer last December. Simon has been quoted as saying his decision to cease touring was influenced by the loss of his old friend. Nguini is replaced by Biodun Kuti, a Nigerian guitarist whose gifts are, thankfully, on a par.

Adding to the plethora of multi-instrumentalists (drummer Jim Oblon plays guitar, guitarist Stewart plays the maui xaphoon, a kind of bonsai sax, Mick Rossi interferes with the strings on his piano) are YMusic, a six-strong New York chamber group of strings and brass. Clustering around Simon for a couple of deep cuts, their input grows in relevance. René and Georgette Magritte With Their Dog After the War (inspired, Simon recounts, by a snapshot in an art book he found at Joan Baez’s house) and Can’t Run But (off Rhythm Of the Saints, 1990) find them playing tensile, abstract rhythms while Simon jazz-raps on top. It sounds like digital R&B played as chamber music from circa 1718.

There are further revelations. The kid who got on the bus in America, says Simon, is the guy working in the carwash on Rewrite, one of the standout songs from 2011’s So Beautiful Or So Whatalbum – one of a series of “ghosts” that move through his songs. Here, Rossi’s prepared piano shimmers out metallic arpeggios.

Controversially, it is probably the Graceland songs that sing the very truest tonight, their cocktail of joy and darkness best expressed by the multitudes on stage. You can’t help but shiver at the line in a transcendent version of The Boy in the Bubble – “The bomb in the baby carriage was wired to the radio” – given what happened here last year.

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And Simon’s reputation as a soft-pop titan (compared to, say, a fellow traveller like Leonard Cohen) does not hold up when you parse certain songs. The Cool, Cool River finds plenty to agonise about. “Sometimes even music cannot substitute for tears,” it concludes, as Rossi finishes off the sentiment with apocalyptic jazz dissonance on the keys.

It all ends, as it must, with The Sound of Silence, the song that changed everything for Simon. He felt “estranged… awkward” about the hit since he gave it to “Artie” to sing. “I’m going to repossess my song,” he says, and physically hugs it to him with his arms. Naturally, it is an offhand, almost Spanish rendition. Undersung from the stage, the backing vocalists in the crowd bellow the canonical version, creating a lingering harmony.